Category: 1137142-58-5

Synthetic Route of 1137142-58-5, These common heterocyclic compound, 1137142-58-5, name is 2-Bromoimidazo[2,1-b][1,3,4]thiadiazole, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Intermediate M; 2-(3,4-Dimethoxy-pheny.)-imidazo[2,1-b][1,3,4]thiadiazoleA solution of 2-bromo-imidazo[2,1-b][1,3,4]thiadiazole (0.5 g, 2.5 mmol, 1 eq), 3,4-dimethoxyphenylboronic acid (0.683 g, 3.7 mmol, 1.5 eq), dioxane (12.5 mL) and Na2CO3 (2M aq. solution, 3.8 mL) was degassed for 20 minutes at room temperature. Pd(Ph3P)2CI2 WaS added and the reaction heated at 110 ºC for 2h in an argon atmosphere. The reaction mixture was diluted with EtOAc and washed with water. The combined organic layers were dried (Na2SO4), filtered and concentrated, and the residue was purified by column chromatography (SiO2, cyclohexane / 20-100% ethylacetate). The product was further purified by triturating with Et2O, filtered off and dried affording the desired product (0.080 g). 1H NMR (300 MHz, DMSO) delta/ppm 8.18 (d, J = 1.4, 1 H), 7.47 (m, 2H), 7.33 (d, J = 1.4, 1H), 7.15 (d, J = 8.3, 1H), 3.86 (s, 3H), 3.75 (s, 3H). – The filtrate was concentrated, redissolved in DCM- and purified by flash-chromatography (SiO2, DCM / 1% MeOH) to afford the desired product (0.65 g, containing some Ph3PO) that was used as such in the next step.

The synthetic route of 1137142-58-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CENTRO NACIONAL DE INVESTIGACIONES ONCOLOGICAS (CNIO); PASTOR FERNANDEZ, Joaquin; KURZ, Guido; MARTINEZ GONZALEZ, Sonia; WO2010/112874; (2010); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

These common heterocyclic compound, 1137142-58-5, name is 2-Bromoimidazo[2,1-b][1,3,4]thiadiazole, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Product Details of 1137142-58-5

Intermediate K2-Bromo-5-nitro-imidazo[2,1-b][1,3,4]thiadiazole; Fuming nitric acid (0.15 mL) was added at 0C to a solution of 2-bromo- imidazo[2,1-b][1 ,3,4]thiadiazole (0.200 g, 1 mmol) in cone, sulfuric acid (0.24 mL), and the mixture was stirred for 5h. Ice was added, and stirring was continued for 30 min. The solid was filtered off, washed with cold water and dried to give the title compound (0.244 g; 83%)1H NMR (300 MHz, DMSO) delta 8.55 (s, 1 H) ppm.

The synthetic route of 2-Bromoimidazo[2,1-b][1,3,4]thiadiazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CENTRO NACIONAL DE INVESTIGACIONES ONCOLOGICAS (CNIO); PASTOR FERNANDEZ, Joaquin; KURZ, Guido; RICO FERREIRA, Maria del Rosario; SOILAN RODRIGUEZ, David; ORTEGA SORET, Miguel Angel; MARTINEZ GONZALEZ, Sonia; WO2011/121317; (2011); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 1137142-58-5, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 1137142-58-5 name is 2-Bromoimidazo[2,1-b][1,3,4]thiadiazole, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Intermediate 23; lmidazo[2,1-b][1,3,4]thiadiazol-2-yl-(4-methoxyphenyl)amine; A mixture of 2-bromo-imidazo[2,1-b][1 ,3,4]thiadiazole (1.0 g, 4.90 mmol) and p- anisidine (19.6 mmol, 2.41 g) in trifluoroethanol (12 mL) was heated under microwave irradiation at 170C for 1 hour. On cooling, the mixture was diluted with dichloromethane (10 mL) and purified by column chromatography (Biotage/Flash, silica, methanol:dichloromethane 0.2:9.8 to 1 :9). The residue obtained was triturated with diethylether and few drops of methanol to give imidazo[2,1-b][1 ,3,4]thiadiazol-2-yl-(4-methoxyphenyl)amine as a white solid (355 mg, 29% yield). 1H-NMR (300 MHz, CDCI3): delta 8.01 (s, 1 H), 7.55 (s, 1 H), 7.44 (d, J = 8.9, 2H), 7.22 (s, 1H), 6.90 (d, J = 8.8, 2H), 3.80 (s, 3H). MS (ES+) m/z 247 (M+H)+ (MW: 246.29).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Bromoimidazo[2,1-b][1,3,4]thiadiazole, and friends who are interested can also refer to it.

Reference:
Patent; CENTRO NACIONAL DE INVESTIGACIONES ONCOLOGICAS (CNIO); WO2009/40552; (2009); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 1137142-58-5,Some common heterocyclic compound, 1137142-58-5, name is 2-Bromoimidazo[2,1-b][1,3,4]thiadiazole, molecular formula is C4H2BrN3S, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Intermediate 19; 2-(4-Fluoro-phenoxy)-imidazo[2,1-b][1,3,4]thiadiazole; A mixture of 2-bromo-imidazo[2,1-b][1,3,4]thiadiazole (1.0 g, 4.90 mmol) and 4- fluorophenol (2.2 g, 19.60 mmol) was heated under microwave irradiation at 135C for 3.5 hours. On cooling, the mixture was diluted with dichloromethane (7 mL), adsorbed in silica and purified by column chromatography (Biotage/Flash, silica, methanol:dichloromethane 0.2:9.8 to 2:8) to give 2-(4-fluoro-phenoxy)- imidazo[2,1-b][1 ,3,4]thiadiazole as a white solid (610 mg, 53% yield).1H-NMR (300 MHz, CDCI3): delta 7.54 (d, J = 1.3 Hz, 1 H), 7.29 (m, 2H), 7.21 (d, J =1.2 Hz, 1 H), 7.14 (m, 2H).MS (ES+) m/z 236 (M+H)+ (MW: 235.24).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Bromoimidazo[2,1-b][1,3,4]thiadiazole, its application will become more common.

Reference:
Patent; CENTRO NACIONAL DE INVESTIGACIONES ONCOLOGICAS (CNIO); WO2009/40552; (2009); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 1137142-58-5,Some common heterocyclic compound, 1137142-58-5, name is 2-Bromoimidazo[2,1-b][1,3,4]thiadiazole, molecular formula is C4H2BrN3S, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Intermediate 30; 2-Bromo-imidazo[2,1-b][1,3,4]thiadiazole-5-suIfonic acid; The starting 2-bromo-imidazo[2,1-b][1,3,4]thiadiazole (2.0 g; 9.9 mmol) was dissolved in oleum (4.0 mL) and the resulting solution was heated at 80C for 8 hours. The reaction was allowed to cool to room temperature and then poured onto crushed ice. One spoon of sodium chloride was added and the resulting precipitate was isolated by vacuum filtration and washed with cold water. It was dried by azeotrope distillation with toluene. The title compound 2-bromo- imidazo[2,1-b][1,3,4]thiadiazole-5-sulfonic acid was isolated as a beige solid, (2.33 g; 83% yield).1H NMR (300 MHz, DMSO-d6): delta 7.30 (1 H, s). MS (ES+) m/z 283.9 (M+H)+ (MW: 218.08).

The synthetic route of 1137142-58-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CENTRO NACIONAL DE INVESTIGACIONES ONCOLOGICAS (CNIO); WO2009/40552; (2009); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 1137142-58-5, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 1137142-58-5 as follows.

General procedure A for the preparation of intermediates 4-8; 2-Bromo-imidazo[2,1-b][1 ,3,4]thiadiazole (1 eq) and the appropriate amine (e.g. cycloprapanemethyl amine) (4.5 eq) were stirred at 135C under microwave irradiation (200W) for 5 minutes. After cooling down to room temperature, the reaction mixture was diluted with dichloromethane and purified by flash chromatography (Biotage , silica, dichloromethane:methanol) to yield the desired product (e.g. cyclopropylmethyl-imidazobeta.i-bj? .S^thiadiazol-2-yl- amine). Intermediate 4 Cyclopropylmethyl-imidazo[2,1-b][1,3,4]thiadiazoI-2-yl-amineThe title compound was obtained in 89% yield.1H NMR (300 MHz, CDCI3): delta 7.27 (brs, 1 H), 7.21 (d, J = 1.3, 1 H), 6.83 (s, 1 H), 3.01 (dd, J = 5.1 , 6.9, 2H), 1.04 – 0.80 (m, 1 H), 0.43 – 0.28 (m, 2H), 0.13 – 0.05 (m, 2H). MS (ES+) m/z 195.10 (M+H)+ (MW: 194.26).

According to the analysis of related databases, 1137142-58-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CENTRO NACIONAL DE INVESTIGACIONES ONCOLOGICAS (CNIO); WO2009/40552; (2009); A2;,
Bromide – Wikipedia,
bromide – Wiktionary